Never used AA before and flying with them this thursday to whistler... I usually always pack my Dakine roller bag with all my gear and some extra clothing, whatever will fit and keep me under 50lbs. I've been doing this for years and never had a problem using Air Canada, West jet, Frontier, Delta..

Just curious if anyone has any experience with American Airlines as I know its technically not supposed to be allowed...

Most airlines seem to have these rules. Very few actually seriously enforce them. I happen to work for an airline and I know that the ticket agents truly couldn't care less so long as you don't go over 50lbs or have any hazardous materials inside. We aren't going to go through your bag counting how many snowboards you are carrying or if you have clothes stashed inside. Thats unless you find that one rare dickhead that thinks he is airline CIA or something